Heat the sugar, water, pumpkin puree and pie spice in a saucepan over medium-low heat. Whisk constantly until the sugar dissolves and let the mixture come to a simmer. Remove it from the heat and let it cool slightly, then add the vanilla extract. Strain it through a fine mesh strainer so you’re left with a syrup consistency. This can be kept in a sealed container in the fridge for a week or so!

Fill a chilled glass with crushed ice and add the pumpkin syrup and bitters over top. Pour in the bourbon and garnish with a cinnamon stick. Serve!